Chiral alignment of OPV chromophores: explitation of the ureidophtalimide based foldamer

R.W. Sinkeldam, F.J.M. Hoeben, M.J. Pouderoijen, I. Cat, de, Jian Zhang, S. Furukawa, S. Feyter, de, J.A.J.M. Vekemans, E.W. Meijer

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Abstract

The ability of foldamers to adopt a secondary structure in solution has been exploited to organize peripheral functionality. Our previously reported poly(ureidophthalimide) foldamer proved to be an excellent scaffold for the chiral organization of peripherally positioned oligo(p-phenylenevinylene) (OPV) chromophores. Facile high-yielding synthesis gave access to the required OPV-decorated building blocks. A condensation polymerization provided polymers of sufficient length to allow construction of a helical architecture comprising several turns. Short and long chains were separated by chromatography. Circular dichroism studies in THF of the longer chains indicate the presence of helically arranged OPVs. However, such an effect is not observed in CHCl3. Remarkable are the measurements of the OPV foldamers in heptane. A bisignate Cotton effect is observed in heptane of a sample with a THF history. No Cotton effect is observed in heptane of a sample with a CHCl3 history. In this example of supramolecular synthesis, the solvent dictates the expression of supramolecular chirality in a secondary structure. The short-chain oligomeric fractions that are unable to create a full turn revealed on scanning tunneling microscopy analysis the presence of circular architectures at the graphite/1-phenyloctane interface. This is in full agreement with the proposed conformation of the decorated foldamers.
Original languageEnglish
Pages (from-to)16113-16121
JournalJournal of the American Chemical Society
Volume128
Issue number50
DOIs
Publication statusPublished - 2006

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Heptanes
Heptane
Chromophores
Cotton
Scanning Tunnelling Microscopy
History
Graphite
Chirality
Dichroism
Scanning tunneling microscopy
Polycondensation
Circular Dichroism
Chromatography
Scaffolds
Polymerization
Conformations
Polymers

Cite this

Sinkeldam, R.W. ; Hoeben, F.J.M. ; Pouderoijen, M.J. ; Cat, de, I. ; Zhang, Jian ; Furukawa, S. ; Feyter, de, S. ; Vekemans, J.A.J.M. ; Meijer, E.W. / Chiral alignment of OPV chromophores: explitation of the ureidophtalimide based foldamer. In: Journal of the American Chemical Society. 2006 ; Vol. 128, No. 50. pp. 16113-16121.
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abstract = "The ability of foldamers to adopt a secondary structure in solution has been exploited to organize peripheral functionality. Our previously reported poly(ureidophthalimide) foldamer proved to be an excellent scaffold for the chiral organization of peripherally positioned oligo(p-phenylenevinylene) (OPV) chromophores. Facile high-yielding synthesis gave access to the required OPV-decorated building blocks. A condensation polymerization provided polymers of sufficient length to allow construction of a helical architecture comprising several turns. Short and long chains were separated by chromatography. Circular dichroism studies in THF of the longer chains indicate the presence of helically arranged OPVs. However, such an effect is not observed in CHCl3. Remarkable are the measurements of the OPV foldamers in heptane. A bisignate Cotton effect is observed in heptane of a sample with a THF history. No Cotton effect is observed in heptane of a sample with a CHCl3 history. In this example of supramolecular synthesis, the solvent dictates the expression of supramolecular chirality in a secondary structure. The short-chain oligomeric fractions that are unable to create a full turn revealed on scanning tunneling microscopy analysis the presence of circular architectures at the graphite/1-phenyloctane interface. This is in full agreement with the proposed conformation of the decorated foldamers.",
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Chiral alignment of OPV chromophores: explitation of the ureidophtalimide based foldamer. / Sinkeldam, R.W.; Hoeben, F.J.M.; Pouderoijen, M.J.; Cat, de, I.; Zhang, Jian; Furukawa, S.; Feyter, de, S.; Vekemans, J.A.J.M.; Meijer, E.W.

In: Journal of the American Chemical Society, Vol. 128, No. 50, 2006, p. 16113-16121.

Research output: Contribution to journalArticleAcademicpeer-review

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AB - The ability of foldamers to adopt a secondary structure in solution has been exploited to organize peripheral functionality. Our previously reported poly(ureidophthalimide) foldamer proved to be an excellent scaffold for the chiral organization of peripherally positioned oligo(p-phenylenevinylene) (OPV) chromophores. Facile high-yielding synthesis gave access to the required OPV-decorated building blocks. A condensation polymerization provided polymers of sufficient length to allow construction of a helical architecture comprising several turns. Short and long chains were separated by chromatography. Circular dichroism studies in THF of the longer chains indicate the presence of helically arranged OPVs. However, such an effect is not observed in CHCl3. Remarkable are the measurements of the OPV foldamers in heptane. A bisignate Cotton effect is observed in heptane of a sample with a THF history. No Cotton effect is observed in heptane of a sample with a CHCl3 history. In this example of supramolecular synthesis, the solvent dictates the expression of supramolecular chirality in a secondary structure. The short-chain oligomeric fractions that are unable to create a full turn revealed on scanning tunneling microscopy analysis the presence of circular architectures at the graphite/1-phenyloctane interface. This is in full agreement with the proposed conformation of the decorated foldamers.

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